Always Lonely: A Visual Celebration of Sinatra

Frank Sinatra will forever be celebrated for his swaggering sense of style, mellifluous singing voice, and intimidating attitude. He was the world’s first modern pop star. But Sinatra’s most important cultural contribution might be what he is known for least: being a trailblazing recording artist. With the release of “In the Wee Small Hours,” in 1955_,_ Sinatra popularized the concept album—a selection of thematically linked songs housed in one package with a unifying cover. Before this influential Sinatra record hit the shelves, songs were packaged and perceived, for the most part, as isolated poetic statements, or “singles.” By curating his albums with songs that told a story he wanted to tell, and by singing each word as if he wrote it, Sinatra introduced a level of personal expression to the recording process that reached literary heights.

The concept album made it easier for the record-buying public to relate to the music that they purchased. Records became friends with whom it was possible to share laughs, ease heartache, and obtain valuable bits of advice. Sinatra recorded fifty-nine studio albums and two live records during his forty-eight-year career. He called “Frank Sinatra Sings for Only the Lonely,” from 1958, his favorite.

One of Sinatra’s most explored themes was loneliness.

Don’t be fooled by the charming smile and the breezy, relaxed pose that Sinatra strikes on the cover of “Nice ’n’ Easy,” from 1960. The title track lives up to its name, but most of the songs are laden with conflict, yearning, and the risks of falling in love.

In 1965, rock and roll was coming of age. The Beatles’ “Help!” and “Rubber Soul_,_” Bob Dylan’s “Bringing It All Back Home,” the Who’s “My Generation,” and the Rolling Stones' “No. 2” and “Out of Our Heads” were all released this year. But the Album of the Year Grammy went to Sinatra for “September of My Years,” his plaintive commentary on the art of aging.

“I was born December 12, 1915,” Sinatra tells the audience during the twelve-minute monologue on the album that he recorded live in a Vegas nightclub with the Count Basie Orchestra. “I was born a very skinny kid,” he says, “so skinny that my eyes were single file.” The monologue, which is titled “The Tea Break,” offers an intimate glimpse of Sinatra’s humor, energy, and bravado onstage. My father, who has listened to Sinatra since he was a boy, told me that if he had to pick one of the singer’s albums to put into a time capsule, “Sinatra at the Sands,” from 1966, would be the one, because it best captures Sinatra at his essence.

Sinatra wasn’t called “The Chairman of the Board” for his vocal cords. He founded Reprise Records, in 1960, so that he could explore whatever kind of musical concepts he wanted to. In 1969, he released “A Man Alone_,_” a collaboration with the poet Rod McKuen, who wrote the words and music. Of the dozen songs on the record, five of them are spoken. The album wasn’t a hit. But it serves as a permanent example of Sinatra’s willingness to take chances as an artist.

Sinatra struck out again the following year, in 1970, with “Watertown_._” Only this record was more of a flop. Produced by Bob Gaudio, who was one of Frankie Valli’s Four Seasons, “Watertown” is the closest thing to a country record that Sinatra ever recorded. An electric guitar playing a cowpoke lick enters eight seconds in, followed by a hokey line about life in a small town that contains two words shortened with a countrified apostrophe—both rare occurrences for a singer of popular standards and a known master of annunciation.

Old Watertown

nothing much happenin’ down on Main

’cept a little rain

But “Watertown” isn’t a country album. It’s a song cycle about the crumbling of a marriage that appropriates country iconography, for better or worse, to convey the setting of the story, which unfolds in a distant, quiet town. Maybe it was the utter embrace of the unfamiliar—no standards, the use of harmonica and jangly guitars, the portrayal of rural life, the rock-and-roll producer, and the lack of anything to do with drinking brandy after hours—that alienated Sinatra’s fans. If Glen Campbell had recorded “Watertown,” the album might have become a classic.

Speaking of drinking brandy after hours, “She Shot Me Down_,_” from 1981, which is largely considered to be Sinatra’s final concept album, is a welcome return to form for the king of torch songs. The only suspension of timelessness is the black Members Only jacket that he dons on the cover.

Sinatra got a lot of flak for using the latest technology to create duets on his last two records, “Duets,” from 1993, and “Duets II,” from 1994. Sinatra recorded alone and then sent his tracks to studios around the world, where his singing partners listened to him in their headphones while they laid down their parts. Some critics wondered if these songs should be considered duets at all. The production method makes me wonder why these releases aren’t considered concept albums, too, with Sinatra having metamorphosed into an actual conceptual artist. Regardless, at the age of seventy-eight, Sinatra was still ahead of the curve. And at no point in his expansive career is the emotion in his voice more palpable than at the end of the last song on the first “Duets,” a medley of “All The Way/One for My Baby (And One More for the Road),” featuring the pop saxophonist Kenny G, who isn’t half bad on this track. But the magic happens after he drops out, along with the rest of the orchestra, when it’s just Sinatra and Bill Miller, the singer’s pianist of more than fifty years. “Man, its long,” Sinatra sings, holding back what sounds like an outpouring of genuine tears, while Miller tickles the song’s famous closing refrain from his ivories for the last time on wax. His boss concludes, “It’s a long, long, long road.”